Water → HCID 118253787, compound

HRID 2201983Notes

Reaction equation

HRID 2201983 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([C:9]([NH2:11])=[O:10])=[CH:4][N:3]=1.CCN(C(C)C)C(C)C.[C:21]([NH2:25])([CH3:24])([CH3:23])[CH3:22].O>CN1C(=O)CCC1>[C:21]([NH:25][C:6]1[C:5]([C:9]([NH2:11])=[O:10])=[CH:4][N:3]=[C:2]([Cl:1])[N:7]=1)([CH3:24])([CH3:23])[CH3:22]

Participants

6

Reactant 4

HCID 962WaterHCID 6385Tert-ButylamineHCID 81531DiisopropylethylamineHCID 212230802,4-Dichloropyrimidine-5-carboxamide

Product 1

HCID 118253787HCID 118253787, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 2,4-dichloro-pyrimidine-5-carboxamide (10.0 g), DIPEA (11 mL) in NMP (30 mL) were stirred at 25° C. tert-Butylamine (6.6 mL) was charged to the mixture, and the mixture was stirred at 25° C. for 16 h. Water (100 mL) was added to the mixture at 25° C. The mixture was stirred for 1 h. The suspension was filtered, washed with water (50 mL) and dried in a vacuum oven at 40° C. with a nitrogen bleed for 24 h to give 4-(tert-butylamino)-2-chloropyrimidine-5-carboxamide as a white solid (8.7 g, 84%). 1H NMR (DMSO-d6) δ 9.41 (s, 1H), 8.55 (s, 1H), 8.19 (s, 1H), 7.67 (s, 1H), 1.42 (s, 9H).

Workup

  1. additionwas charged to the mixture
  2. stirringThe mixture was stirred for 1 h
  3. filtrationThe suspension was filtered
  4. washwashed with water (50 mL)
  5. customdried in a vacuum oven at 40° C. with a nitrogen
  6. waitbleed for 24 h

Sources & evidence

ORD record
ord-5a36db240ad646a691985eb762a8cc24
Source dataset
uspto-grants-2016_06
Patent number
US09365524B2

Reaction notes

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